About
I've sat in your chair.
I lead marketing for owner-led service businesses the way I'd want my own led, because I've built and run several myself.
Jessica Roubitchek, MBA · Founder
An operator first.
My strategic foundation began with my MBA from the University of Chicago Booth School of Business. For over a decade since, I've advised service businesses while building, scaling, and exiting my own.
I built Purple Monkey Playroom from an empty storefront into a destination families drove across the city to visit. When we outgrew capacity, I avoided double-competing in a saturated market and opened a complementary event venue instead. I know what it takes to drive demand, manage capacity, and make hard calls.
After my exit, I saw a recurring gap in my consulting work: owners didn't need another strategic plan—they needed execution. I shifted to fractional leadership to step past giving advice and actually own the outcome.
Along the way, I grew local networking communities to nearly a thousand members and co-founded the W.Edge Collective, a team of fractional executives.
That combination—a trained strategist who is an operator first—is what I bring to your marketing. Because I've handed off work carrying my own name, I know the line between taking weight off your plate and taking decisions out of your hands. I bid work with no vendor conflicts of interest, using my implementation partners or yours.
I'm a Chicagoan, married, and raising a teenager and two dogs. I know what running a demanding business and a life requires, which shapes how I work: directly, efficiently, and focused on what matters.
I lead from your side of the table. You stay in control. I carry the weight.
Core principles
I don't believe every problem needs advertising.
I don't believe every business needs SEO.
I don't believe marketing should create work for the owner.
I believe growth happens when the right levers are pulled in the right order.
Beyond client work
Speaking and press.
Speaking topics
I speak at conferences, corporate events, and professional networks on strategic marketing, habit-driven growth, customer-centric brand building, and visibility for service businesses.
As featured in
Articles, interviews, and features on marketing, growth, and fractional leadership.
The team
Dami Gold
Executive Assistant
Dami keeps things moving behind the scenes. She coordinates meetings with Jessica, keeps client projects on track on the back end, and stewards select engagements so nothing slips between conversations. For clients, that means the work keeps progressing between strategy sessions, and the details are handled without anything landing back on your plate.
Known for her reliability, initiative, and attention to detail, Dami is the reason the function runs smoothly day to day. Her growing focus on operations and business growth shows up in the systems and rhythms she builds to give leaders more capacity for what matters most.